In this series,The Gambit, Entrepreneur associate editor Hayden Field explores extraordinary risk, speaking with successful people about how they overcame unusual obstacles to found a company or switched industries entirely in a "career 180."

For two hours and 15 minutes, Nelson Mandela’s eyes were fixed on a screen that told his story.

It was 2009, and Mandela was seated in his namesake foundation’s screening room in Johannesburg, South Africa. The film was Invictus, and he was riveted. At some points, Mandela laughed. Other scenes made his eyes fill with tears. All the while, the film's producer Lori McCreary watched him as he watched his own portrayal.

McCreary remembers Mandela turning around after the film’s conclusion and saying, “Now, perhaps, people will remember.” It was one of the most powerful moments of her filmmaking career.

McCreary is CEO of Revelations Entertainment, a production company she co-founded with actor Morgan Freeman (who is currently facing allegations of sexual harassment -- McCreary did not respond to a request for comment about the allegations), and co-president of the Producers Guild of America. But her career path was anything but traditional. More than two decades earlier, McCreary graduated with a computer science degree and made coding her full-time job.

The Itch

McCreary discovered her love of storytelling at 8 years old, when her actress mother signed her and her siblings up for community theater in Antioch, Calif. She did six shows per year through middle and high school, and at 15, she decided she would one day own a theater and earn her living by telling stories.

Before graduating high school, McCreary spent her free time serving as technical director of an Antioch theater. The city had recently invested more than $1 million in the space and its newfangled features, including a computerized lighting and sound board. Personal computers weren’t mainstream yet, but McCreary’s father had one of the first iterations at home. She took it upon herself to learn how to work the board for an upcoming musical, The Boy Friend -- a romantic spoof of 1920s musical comedies.

McCreary had originally learned to program lighting cues on a manual board, so having a computerized one felt like freedom -- she could even program an intricate five-minute-long sunrise. (If she’d wanted the same effect from the old lighting board, she’d have to sit there and manually move the switches for five minutes straight.)

But when opening night came, excitement turned to panic. She walked into the tech room, turned on the computer and … nothing happened. McCreary immediately entered action mode. She transferred everything back to the manual board, and though the show did go on, the lighting cues didn’t work as well because they were designed for the computer.

Shortly afterward, while filling out college applications, McCreary paused before filling in “theater” as her major. I’ve done theater for 10 years, she thought. Maybe I should do this computer thing.

It wasn’t long before McCreary felt technology was already influencing storytelling in a significant way, and she wrote an in-depth paper on the convergence of technology and the entertainment industry. At the University of California, Los Angeles (UCLA), she tried to create a major combining computer science and theater, but the two different schools -- fine arts and computer engineering -- didn’t support the overlap. Someone suggested she switch back to theater, but McCreary resisted. She felt she had to master computer science in order to better tell stories, so she settled for high-level theater electives.

Before graduating in 1984, McCreary had the chance to work on a collaborative project between the computer science program and the theater department: building in machine language to help move the UCLA theater’s motorized lighting system. The motors were already connected to the theater lights, but McCreary’s job was to figure out how to effectively communicate the digital signals to the lights so they would use the cues to move on their own.

Many people didn’t make it through the first year of the computer science program, but McCreary loved the idea of creating something from nothing -- thinking up an idea, building it with software and releasing it into the world for people to use.

Image credit: Lori McCreary

The Detour

McCreary worked part-time at a store called ComputerLand to help pay for college, and one day, a man came in with an Apple II series computer -- chunky, 8-bit and off-white. The man, David Kalmick, showed McCreary a piece of software that was interesting but slow, and she told him how to make it faster (step one: switch to a PC). McCreary started working for Kalmick and his wife part-time and helped them launch CompuLaw, which created software that helped lawyers track their time and bill clients more efficiently.

After graduation, law software became McCreary’s full-time gig. At the time, little new software was being created, so anyone who was putting out new product had a chance of making it big -- including CompuLaw. McCreary coded a new interface for connecting a handheld computer to a copier -- and created a “B-tree library” to speed up access time for lawyers searching for client names in the system. (Before, lawyers had to manually scroll through each client name alphabetically until they landed on the one they were looking for.) She also traveled around the country to teach lawyers how to use the software.

One night in her office, McCreary had an epiphany. She was fixing lines of code at her desk around 11 p.m. and suddenly thought: Is my epitaph going to say, "Lori McCreary: She helped lawyers bill people more efficiently"? She wondered how she got there. Yes, she loved her partners and teaching people how to use computers, but she didn’t feel it was feeding her soul.

“I came from storytelling,” she says. “I came from a place where you go into the room, the lights would go down and people would come out transformed.” She missed having that kind of effect on people.

McCreary told Kalmick and his wife she was leaving the company to go into theater, and though they responded graciously, they were also shocked -- they had both grown up in California and knew how hard it was to make it.

The Leap

After leaving CompuLaw, McCreary decided to work with a lawyer-slash-theater producer she knew, Larry Taubman, to bring a musical playing in London’s West End over to the U.S. To pay the bills, she worked as a software and computer consultant on the side. (One of these side gigs was helping famed musician Frank Zappa put together a database and connect a printer to his synthesized piano.)

McCreary and Taubman hopped on a plane to London to work on bringing the musical over, but they soon learned that one of the authors had died, putting everything on hold. For two weeks in London, the two played the waiting game -- and as theater enthusiasts, they chose to wait by seeing show after show in the West End. Everything changed when they sat down in the National Theater to see a fringe festival play called Bopha! The story features two South African brothers -- one a police officer enforcing apartheid, the other part of the resistance. McCreary and Taubman watched as every member of the audience stood up after the play’s conclusion, raised their fists in the air and shouted, “Bopha!” They knew immediately they had something special on their hands.

McCreary remembers turning to Taubman and saying, “More people need to see this.”

“We should turn this into a movie,” he replied.

“Do you know how to make a movie?”

“It can’t be that much harder than theater.”

The plan was in motion.

McCreary and Taubman decided to launch a company called Cinecity Pictures solely to produce Bopha! After landing back in the U.S., she says they went to a bookstore and bought every book they had on filmmaking. Taubman did the legal work, and McCreary took over optioning the material. The two called up the play’s author, Percy Matwa, in South Africa -- he agreed to sell them the rights, but even though the fee was cheap relative to the standard, it still seemed like a lot of money to McCreary at the time. The next step was hiring writers -- and soon the screenplay was real, and she held it in her hands.

Image credit: Lori McCreary

The Breaking Point

McCreary thought they had an incredible script. She couldn’t read it without crying. And she and Taubman sent it off to every film studio they could think of.

It was, ultimately, a bust. McCreary and Taubman were left with two filing drawers filled with rejection letters. She remembers reading comments including, “I cried when I read it, but it’s not for us.”

That went on for two years.

Finally, a production lawyer suggested they connect with a group called Artists for a Free South Africa, and after meetings, McCreary realized star power was what they needed to get Bopha! off the ground. She pictured Morgan Freeman as the perfect lead, so she mailed the script to his agent.

It wasn’t long before the phone rang.

“Morgan was just thinking about what he would do when they stopped calling him to act, and he thought he might want to direct,” McCreary remembers the agent saying. “Would you be interested in Morgan directing?”

McCreary said yes while trying to keep her cool. Danny Glover was suggested for the main role. And right away, she chanced jumping the gun, calling Glover’s agent and telling him that Morgan Freeman was directing the film and he wanted Glover to play the lead. Glover was in, and McCreary started re-pitching the film with the added star power.

Studios still wouldn’t bite.

“I cried,” she remembers reading in even more rejection letters. “This is such a story that needs to be told … but … pass.”

It had been years since that night at the National Theater in London, and the two were growing discouraged. It was the late 1980s -- McCreary was still working as a consultant, and Taubman was still practicing law on the side.

The Turnaround

It was another late night in the office -- again, around 11 p.m. -- when things changed again for McCreary. Taubman called to say he was on a blind date, and his date happened to work for actor and talk show host Arsenio Hall. She was interested in Bopha!

It was music to McCreary’s ears. She messengered the script over immediately, and in less than three days, she and Taubman had a meeting with Hall himself.

“Arsenio wants to see you at 11 in the morning -- and he doesn’t usually come in before 2,” McCreary remembers hearing.

Hall told them he loved the script. His talk show was peaking, and he said Paramount owed him three movies and he wanted Bopha! to be one of them.

After six years, McCreary could finally see the finish line. A couple of weeks later, she and Taubman signed a deal with Paramount Pictures. They had a $12 million budget and plans to shoot on location in Zimbabwe.

The only problem: Colleagues told McCreary that now that they’d hit the big-time, she and Taubman definitely wouldn’t get the green light to work as the film’s producers. “They’re not going to send you and Larry with a first-time director -- Morgan Freeman -- with $12 million in the middle of Africa,” she remembers hearing.

McCreary had never thought of that. But when a Paramount executive called her and Taubman into his office with an entire sheet of questions, she was able to wing it -- with the help of her portable computer and an early version of Movie Magic software for scheduling and budgeting.

“You have too many grips,” he told her. She didn’t know what a grip did at the time, but she used the software to search for the word, type in a smaller number and calculate the potential savings: $40,000 a week. He wrote down the figure. Then he asked about cutting down the number of production days from 68 to 63, and she calculated those savings. Because McCreary knew how to work a computer and budgeting software, “they thought I was a mad producing genius,” she says.

The next thing she knew, she and Taubman were on their way to Zimbabwe without a so-called “real producer” in sight. She felt both pleased and petrified. The two stayed up late every night to figure out what a “DP” did and what a “gaffer” was. One of their tricks: mapping out the parallels between film production and theater production.

When McCreary walked onto the Bopha! set in Zimbabwe, she knew being a producer was the perfect intersection of her interests in technology and storytelling. By the time the cameras started rolling, it had been seven years since that night at London’s National Theater. Later on, when McCreary launched her new company with Morgan Freeman, Revelations Entertainment, she would carry that idea with her: Only take on a project if you’re willing to work on it for seven years. That way, you know you love a story enough to stay the course.

Image credit: Lori McCreary

The Next Step

McCreary had the chance to show Bopha! to Nelson Mandela about three years after he was released from prison -- and just before his election as president of South Africa. She remembers him coming up to her and saying, “This is a very important film.”

“I could’ve been done with filmmaking at that moment,” she says.

The inspiration for Invictus, the film she produced about two decades later, struck McCreary around that time. After working with Freeman, she thought the two men had a similar “spirit” and imagined Freeman playing Mandela in a story of his life. In 2009, that idea would come full circle, as the president of South Africa watched her film about his country coming together instead of the story of the movement that tore it apart.

About a quarter of the Bopha! crew members went on to work on Invictus, but within two decades, they had risen from production assistants to running entire departments. And this time around, McCreary and Freeman were producing partners -- running their own company focused on timeless stories.

Revelations Entertainment recently celebrated its 20th anniversary. “We started this company in part to do stories about people that look like me and people that look like Morgan,” McCreary says. McCreary says that in light of a recent societal and cultural shift, she’s finally getting calls about projects they’ve had in the pipeline for more than seven years. McCreary finds it heartening that the market is opening up to stories about all kinds of people.

As for advice for others looking to make a leap? “You will never be younger than you are now,” she says. McCreary took a pay cut to both switch into production and start her company with Freeman, but she wouldn’t trade it for sitting at that computer at 11 p.m. thinking about what her epitaph would say.

“It’s scary, but for me, I had more joy at the end of a day working on something that I knew was feeding my soul,” she says. “Go into what’s soul-filling … the money will eventually catch up.”

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